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“Click” reactions in polysaccharide modification
Affiliation:1. Macromolecules and Interfaces Institute, Virginia Tech, Blacksburg, VA 24061, United States;2. Department of Sustainable Biomaterials, Virginia Tech, Blacksburg, VA 24061, United States;1. Biomedical Materials Group, Institute of Pharmacy, Martin Luther University Halle‐Wittenberg, Heinrich‐Damerow‐Strasse 4, D‐06120 Halle (Saale), Germany;2. Interdisciplinary Center for Material Research & Institute of Physics, Martin Luther University Halle-Wittenberg, Heinrich-Damerow-Strasse 4, 06120 Halle (Saale), Germany;3. Institute of Plant and Wood Chemistry, Dresden University of Technology, Pienner Strasse 19, D‐01737 Tharandt, Germany;4. Heppe Medical Chitosan GmbH, Heinrich-Damerow-Strasse 1, 06120 Halle, Germany;1. Macromolecules and Interfaces Institute, Virginia Tech, Blacksburg, VA 24061, USA;2. Department of Sustainable Biomaterials, Virginia Tech, Blacksburg, VA 24061, USA;3. Department of Chemistry, Biochemistry and Physics, Niagara University, Lewiston, NY 14109, USA;4. Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA;1. Macromolecules and Interfaces Institute, Virginia Tech, Blacksburg, VA 24061, United States;2. Department of Sustainable Biomaterials, College of Natural Resources and Environment, Virginia Tech, Blacksburg, VA 24061, United States;3. Department of Chemistry, College of Science, Virginia Tech, Blacksburg, VA 24061, United States;2. Department of Cell Biology and Histology, Faculty of Medicine and Dentistry, University of the Basque Country, Barrio Sarriena s/n, 48940 Leioa, Spain;1. Macromolecules and Interfaces Institute, Virginia Tech, Blacksburg, VA 24061, United States;2. Department of Sustainable Biomaterials, College of Natural Resources and Environment, Virginia Tech, Blacksburg, VA 24061, United States;1. Istituto Italiano di Tecnologia, IIT@CRIB, Largo Barsanti e Matteucci 53, 80125 Napoli, Italy;2. Università degli Studi di Napoli Federivo II, Centro di Ricerca Interdipartimentale sui Biomateriali, CRIB, Piazzale Tecchio 80, 80125 Napoli, Italy;3. Università di Napoli Federico II, Dipartimento di Chimica, via Cintia, 80126 Napoli, Italy
Abstract:Polysaccharide chemistry is enjoying accelerating development thanks to advances in synthetic techniques, biochemistry and solvents, which enable polysaccharide materials to be useful in a variety of demanding applications. Among the synthetic advances, click chemistry has reconfigured the realm of polysaccharide modification that previously was dominated by conventional synthetic approaches such as esterification and etherification. “Click” reactions provide mild, modular, and efficient modification pathways, and equally importantly allow us to synthesize derivatives with novel functionality, architecture, and properties, that are otherwise difficult to obtain via conventional methods. Herein, we review application in polysaccharide modification of six groups of click reactions; CuAAC (copper catalyzed alkyne/azide cycloaddition), metal-free 3+2] cycloaddition, Diels–Alder reaction, oxime click, thiol-Michael reaction, and thiol-ene reaction, as well as one click-like reaction that is the subject of our own research, olefin cross-metathesis.
Keywords:Click chemistry  Polysaccharide  Chemical modification  Hydrogel  Drug delivery  Olefin metathesis
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